Sodium Carbonate → 6-(Quinoxalin-6-yl)-N-(4-(trifluoromethyl)phenyl)pyrimidin-4-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-N-(4-(trifluoromethyl)phenyl)pyrimidin-4-amine (273 mg, 1.0 mmol), benzopyrazine-6-boronic acid hydrochloride (Asymchem, 211 mg, 1.0 mmol), Na2CO3 (529 mg, 5.0 mmol) and PdCl2(PPh3)2 (Strem, 60 mg, 0.1 mmol) in 7 mL DME/3 mL H2O/2 mL EtOH was heated to 120° C. for 17 min in the Smith Optimizer microwave. The reaction mixture was partitioned between EtOAc/brine and the aqueous layer was extracted with EtOAc (3×). The combined organics were evaporated onto SiO2 and purified by flash column chromatography eluting with EtOAc/Hexane/2M NH3 in MeOH/CH2Cl2 (0:1:0:0→1:1:0:0→0:0:19:1). The fractions containing desired compound were combined and concentrated in vacuo giving a solid. The solid was washed with a minimal amount of CH2Cl2 and dried in vacuo to give a light pink amorphous solid. MS (ESI, pos ion.) m/z: 368 (M+1).

Provenance & Evidence